Watch Sailing & Boating Adventures Around the World

Explore sailing, boating, and water sports through our curated video archive. From epic sea voyages to serene diving escapes, discover unforgettable adventures from top YouTube creators. Start your journey. Dream big. Sail far.

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I Finally Sailed to Maui — Where It All Began
Sailing With Phoenix | Oliver

I Finally Sailed to Maui — Where It All Began

We set sail from Hilo to Maui with light winds 90% of the way, finally catching a chill downwind run. I reflect a little bit on why I love sailing so much and how the hard work does eventually pay off. After arriving in Lāhainā we battle surf breaks to get the dinghy ashore and then hike a wild loca...
Sailing 220 Miles From Oahu to the Big Island
Sailing With Phoenix | Oliver

Sailing 220 Miles From Oahu to the Big Island

A 220-mile sail from Oahu to the Big Island became a lesson in patience and respect. Between calm seas and sudden squalls, we were forced to change course — the sea had other plans. ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s Phoenix Now? 👕 Official Merch 📸 Instag...
Sailing the Wrong Way across the Alenuihaha Channel from Maui to the Big Island on a 30ft Sloop
Sailing Triteia

Sailing the Wrong Way across the Alenuihaha Channel from Maui to the Big Island on a 30ft Sloop

Episode #252 : Season 8 : The Hawaiian Adventures Hello Friends, On this episode @kimberlywood-saltybutterfl262 and myself make passage across the dreaded Alenuihaha Channel between Maui and the Big Island of Hawaii. After an easy but very wet passage we arrive at Nishimura Anchorage and enjoy s...
WE Sail from the Big Island to Maui Overnight | Episode 122
WE|Sail

WE Sail from the Big Island to Maui Overnight | Episode 122

Aloha Big Island, Aloha Maui. WE set sail from the Big Island to Maui for an overnight passage across the Alenuihaha Channel, known as one of the most dangerous passages. Luckily for us, we paid close attention to the weather and chose to go at night as the winds typically soften through the gap. ...
WeBoating
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